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Flying First Date

I met a guy online a few weeks ago and we've had a great time emailing each other and talking on the phone and on Skype. He's Jewish, he's smart, he's funny, he has a great career and he's good looking. I'm excited to meet him in person, but the problem is that he lives too far away to visit without flying. Typically, I would say that long distance relationships are not for me. But I've been thinking of relocating anyway, and I haven't been having the best dating luck in Philly. We've been talking about flying to a city where neither of us lives for a weekend date. Is this crazy?

Signed,
Flying First Date

Dear Flying,

Last year, I wrote a column about long distance relationships. All of that advice still holds true for you, but you have the added dimension of not having actually met this person. Sure, it's probably a little crazy to meet this guy and think about starting something long distance with someone who is ultimately still a stranger. However, that doesn't necessarily mean you shouldn't do it. People do lots of crazy things. Sometimes they work out and sometimes they don't, but they usually make for a good story. As long as you are 100 percent positive that meeting this guy will be safe — he is who he says he is, you'll be meeting in a public place for the first time, you make solo sleeping arrangements, etc. — then I say go for it. Bonus points if you have friends in this neutral city, so if any number of parts of your plan don't work out, the trip won't be a total bust.

You should also go into the experience with an open mind and a "wait and see" attitude, rather than getting your hopes up so high that even if he's almost perfect, you're bound for disappointment. Online dating is an amazing tool and lots of fabulous relationships have come from it, but so have lots of broken hearts belonging to people who start planning their 10-year anniversary party before they've ever held hands. Skype is also a great tool, but it's not the same as meeting someone in person. So even though you've had some great talks, you don't really know someone until you're in the same room for a while. Even then, maybe it takes months or years, but that's a topic for another day.

You say that dating in Philly hasn't been going so well, so even if things with this guy don't go anywhere, it could be a nice confidence boost to find out that there are great guys out there (provided he turns out to be great, of course). Since he's not connected to your current life, this kind of no-strings-attached date also gives you permission to try out who you really want to be when you meet someone for the first time. That, in turn, could help you approach dating with a new attitude back home. Just remember that he has the same freedom, so you're probably not getting the full picture of him right away, either.

If you decide to go for it, try to live in the moment when you're there. Enjoy his company instead of spending the whole time wondering if you'll ever see each other again, if the whole trip was a mistake, if you'd be willing to move to be close to him or if he lives up to his profile. This is just one weekend, so try not to make it about the rest of your life. If things don't work out, it's just one bad weekend and you'll get over it. If it's the best weekend of your life, you'll know that you made a good decision and that both of you have many more decisions in front of you to make the relationship work.

Safe travels and be well,
Miriam

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Ask Miriam Steinberg-Egeth, a local mom and involved member of Philadelphia's Jewish community. Wondering what's an appropriate gift for a Bar Mitzvah? How to deal with an annoying friend/parent/relative? How to find your soulmate? From dating to parenting, Miriam welcomes any and all questions. Email yours to [email protected] and put "Advice Well question" in the subject line. More from this author